An Extremely Mild, Convenient Procedure for the Reduction of Sulfoxides to Thioethers

Synlett

Volumn 1996, Issue 9, 1996, Pages 885-886

  Wang, Yamin ^a   Koreeda, Masato ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001999045     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5613     Document Type: Article

References (23)

1. 3COOH: Nicolás, E.; Vilaseca, M.; Giralt, E. Tetrahedron 1995, 51, 5701-5710.
2. 3COOH: Nicolás, E.; Vilaseca, M.; Giralt, E. Tetrahedron 1995, 51, 5701-5710.
3. 3COOH: Nicolás, E.; Vilaseca, M.; Giralt, E. Tetrahedron 1995, 51, 5701-5710.
4. 3COOH: Nicolás, E.; Vilaseca, M.; Giralt, E. Tetrahedron 1995, 51, 5701-5710.
5. 3COOH: Nicolás, E.; Vilaseca, M.; Giralt, E. Tetrahedron 1995, 51, 5701-5710.
6. 3COOH: Nicolás, E.; Vilaseca, M.; Giralt, E. Tetrahedron 1995, 51, 5701-5710.
7. 3COOH: Nicolás, E.; Vilaseca, M.; Giralt, E. Tetrahedron 1995, 51, 5701-5710.
8. 3COOH: Nicolás, E.; Vilaseca, M.; Giralt, E. Tetrahedron 1995, 51, 5701-5710.
9. 3COOH: Nicolás, E.; Vilaseca, M.; Giralt, E. Tetrahedron 1995, 51, 5701-5710.
10. 3COOH: Nicolás, E.; Vilaseca, M.; Giralt, E. Tetrahedron 1995, 51, 5701-5710.
11. 3COOH: Nicolás, E.; Vilaseca, M.; Giralt, E. Tetrahedron 1995, 51, 5701-5710.
12. 3COOH: Nicolás, E.; Vilaseca, M.; Giralt, E. Tetrahedron 1995, 51, 5701-5710.
13. 3COOH: Nicolás, E.; Vilaseca, M.; Giralt, E. Tetrahedron 1995, 51, 5701-5710.
14. Reviews: (a) Barbachyn, M. R.; Johnson, C. R. In Asymmetric Synthesis: Morrison, J. D.; Scott, J. W., Eds.; Academic Press: New York; 1984; Vol. 4, Chapter 2. (b) Seyden-Penne, J. "Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley & Sons; New York: 1995; pp 78-81. (c) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
15. Reviews: (a) Barbachyn, M. R.; Johnson, C. R. In Asymmetric Synthesis: Morrison, J. D.; Scott, J. W., Eds.; Academic Press: New York; 1984; Vol. 4, Chapter 2. (b) Seyden-Penne, J. "Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley & Sons; New York: 1995; pp 78-81. (c) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
16. Reviews: (a) Barbachyn, M. R.; Johnson, C. R. In Asymmetric Synthesis: Morrison, J. D.; Scott, J. W., Eds.; Academic Press: New York; 1984; Vol. 4, Chapter 2. (b) Seyden-Penne, J. "Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley & Sons; New York: 1995; pp 78-81. (c) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
17. Koreeda, M.; Yang, W. Synlett. 1992, 201-203. J. Am. Chem. Soc. 1994, 116, 10793-10794.
18. Koreeda, M.; Yang, W. Synlett. 1992, 201-203. J. Am. Chem. Soc. 1994, 116, 10793-10794.
19. 2: C, 43.46; H, 4.38. Found: C, 43.08; H, 4.45.
20. Commercial zinc dust was activated by washing with 2% aqueous HCl (see: Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon Press: Oxford; 1988; p. 360).
21. Representative procedure: To a stirred solution of methyl phenyl sulfoxide (3) (70 mg, 0.50 mmol), acetic anhydride (0.10 mL, 1.0 mmol), and DMAP [(4-dimethylamino)pyridine] (6 mg, 0.05 mmol) in 3 mL of dry acetonitrile was added activated zinc (327 mg, 5.0 mmol) at room temperature. The resulting mixture was stirred at that temperature for 12 h, upon which time the mixture was diluted with 15 mL of diethyl ether and the resulting insoluble material was removed by filtration. The filtrate was washed first with saturated aqueous sodium bicarbonate (10 mL) and then with brine (10 mL). The organic layer was dried over anhydrous sodium sulfate and the solvent was removed by rotary evaporation. The resulting colorless oil was purified by silica gel flash column chromatography using 6 : 1 hexanes/ethyl acetate as the eluent, providing 59 mg of thioanisole (4) (95%).
22. Ishibashi, H.; Komatsu, H.; Ikeda, M. J. Chem. Res. (M) 1987, 9, 2548-2561.
23. A trace amount of reduction product 4 (5%) was formed after 20h at room temperature.